5-Aza analogs were prepared of several tryptamine derivatives and a skatole derivative known to bind at human 5-HT6 receptors and evaluated to determine if they bind in a manner similar to their indolic analogs. In general, the azatryptamines did not behave exactly like their tryptamine counterparts, but the behavior of N1-benzenesulfonyl analogs was reminiscent of the known arylsulfonyltryptamines. For example, N1-(4-aminobenzenesulfonyl)-5-azaskatole (18; Ki ≡ 41 nM) displayed an affinity comparable to N1-(4-aminobenzenesulfonyl)skatole.